Sodium Bicarbonate → 4-(2-Pyridylsulfonyl)aniline

HRID 327169Notes

Reaction equation

HRID 327169 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)(=[O:9])=[O:8].C(=O)(O)[O-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)(=[O:8])=[O:9]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 214801062-(4-Nitrobenzene-1-sulfonyl)pyridine

Product 1

HCID 105138504-(2-Pyridylsulfonyl)anilineYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4-nitrophenyl 2-pyridyl sulfone (6.50 g, 24.6 mmol) and stannous chloride dehydrate (27.72 g, 123.0 mmol) in absolute ethanol (200 mL) was heated at reflux for 25 min. The reaction mixture was poured into ice water, and the aqueous solution basified with sodium bicarbonate (pH=8-9) and extracted with ethyl acetate (2×400 mL). The organics were combined, dried (MgSO4), filtered, and the solvent distilled to yield the title benzenamine (5.12 g, 89%) as a white solid; mp 158°-160° C. 1H--NMR (300 MHz, d6 --DMSO): 6.27 (broad s, 2H, NH2), 6.66 (d, 2H, J=8.7 Hz, aromatic), 7.61 (m, 3H, aromatic), 8.08 (d, 2H, J=4.9 Hz, aromatic), 8.68 (d, 1H, J=4.9, aromatic). MS (CI, CH4): 235(M+1).

Workup

  1. temperatureat reflux for 25 min
  2. extractionextracted with ethyl acetate (2×400 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. distillationthe solvent distilled

Sources & evidence

ORD record
ord-757bf85642a146bcae03d6c263070845
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

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